It doesn’t have to be an unpleasant process, though. Here are some ways to keep your sanity take the horror out of new software training and implementation:

Get It Right The First Time

Your attempts at onboarding will stop before they begin unless you make sure to select an appropriate tool in the first place. Buy something before you’re completely certain it can handle your specific requirements, and you’ll be left with a very expensive doorstop (or a monthly stupid-tax, if you’ve opted for an SaaS subscription). That said, there are a lot of project management systems out there these days, and it can be difficult to know where even to begin when selecting new software. The process will be much easier if you take the time to consider these questions:

Do you want the new software to replace your existing communication systems, or just integrate with them? Many modern project management programs integrate smoothly with Gmail or Outlook, but you may want to just replace email altogether. If you keep all conversations, files, and assignments within the bounds of the software, then nothing gets lost or overlooked. Plus, that way everything is searchable, easily accessed, and can be archived for future reference.

Does the new software need to integrate with tools you’re already using? If your company relies heavily on file sharing programs like Box or Dropbox, you better make sure any potential project management systems do too. Take a good hard look at your current accounting, CRM, and email marketing software as well. Not all project management vendors offer robust integrations, but most of them at least give you the option to create your own using an API. If the software you’re considering doesn’t integrate with other popular tools or give you access to an open API, run the other direction.

What features are you looking for? Before you buy anything - before you even start looking for a new tool - sit down and write out a comprehensive list of must-haves. Do you just need a simple task manager that gives you a place to communicate and store files? Or are you looking for something that will actively manage employees, the budget for projects, and track time spent on assignments? How about scheduling - do you want to schedule by hand or have the software do it for you? Does your team use a specific project management system like Waterfall, Agile, or Kanban? Are video conferencing or shared document editing important to you? Get your priorities straight first, and the selection process will be much less frustrating.

What can you afford to pay per month? This may go without saying, but I’m going to say it anyway. Don’t buy anything in life unless you’re certain you can afford it. This is just as true for project management software as it is for cars, homes, and electronics. The consequences of ignoring reasonable budget guidelines are often embarrassing, usually uncomfortable, and always painful.

Do you want on-premise software, or a cloud-based SaaS (software-as-a-service)? Locally installed project management systems will give you immediate control over your data and can be (arguably) more secure, but cloud-based options, which usually offer automatic updates and free customer service, are often cheaper and more convenient. Government agencies, banks, financial institutions, etc. tend to prefer on-premise software because it gives them greater control over the safety of their information; most standard businesses, however, are probably better off with SaaS.

Provide Incentives

People don’t like change. Unless they’re particularly chipper and adventurous, most of your employees won’t want to learn a new program; they’re very happy with the old system, thank you very much. So if you want them actually to use expensive new software, you’d better give them a darn good incentive. Some managers find that positive reinforcement works wonders, but in truth, the best way to get your employees invested in a different system is to penalize them for backsliding into old habits. That may seem harsh, but after all, what good is an ultra-modern, feature-rich project management system to you if even a quarter of your employees are still trying to communicate via email, casual conversations by the water cooler, and Post-It notes?

Relax. I’m not suggesting that you start handing out pink slips or drag offenders off to the office pillory. Sometimes it’s enough to simply ignore rogue communications. All but the most thick-skinned employees usually begin to catch on after a few snubbed emails. If you’re not that passive aggressive, you can simply respond to non-sanctioned status updates, file shares, and discussions with a gentle reminder to do official business within the confines of the project management software.

Take Advantage Of Training Opportunities

All the incentives in the world won’t help your people much if they just don’t know how to use the new software. Many basic task managers, like Basecamp, Trello, and Asana, are fairly intuitive, but others - Smartsheet, LiquidPlanner, and PivotalTracker come to mind - come with a steep learning curve and require a serious investment in training and education. And even the simplest programs can be hard to figure out sometimes. Fortunately, there are a few things you can do to facilitate the learning process:

Use the training materials provided by your software vendor. Any project management program worth its salt will give you access to video tutorials, webinars, FAQs, community forums, white papers, and a detailed knowledge base. Make sure people know where to find help if they need it.

Let employees know it’s okay for them to initiate contact with customer service. Your workers shouldn’t have to wait for you to fix bugs or answer questions. Many project management vendors offer 24/7 technical support, and most of them at least provide support services during normal business hours. Live chat and phone support are the quickest ways to get help with any problems that might crop up, but email queries and/or service tickets work well too and give you the added benefit of being able to add screenshots to illustrate your problem.

Shell out for extra training options. A lot of vendors provide premium support services - dedicated account managers, on-site employee training sessions, system set-up and integration, etc. - for an added fee. Unless you’re very confident in your own abilities, it’s usually a good idea to take advantage of vendor assistance; after all, who knows the program better than they do?

Designate an on-site expert. It may not be financially feasible for you to pay for a dedicated account manager or premium vendor-provided training. In that case, you’d do well to select one or two people from your company to become “experts” in the new software. Give them time to read all the training material, take any available webinars, and play around with the software. Part of their work duties going forward can be to handle problems with the software, teach others how to perform complex functions, etc. In that case, everybody wins. You gain an expert or two who know the software back and forwards and have a good handle on the inner workings of your specific business, and the rest of your employees receive on-the-job training.

Onboarding new project management software is hard, but it doesn’t have to make you crazy. There’s really no need to stress; take a deep, cleansing breath and tell yourself that everything is going to be okay. Start things out right by choosing an appropriate tool. Then ensure your team is invested and willing to use the new software, and take advantage of available training materials and opportunities, and you’ll be well on your way to a successful implementation. Good luck!

Julie Titterington is the Managing Editor of Merchant Maverick, an SMB software and services review site. Her expertise extends to many areas of small business technology, but she specializes in project management software systems. Julie lives in Portland, OR and spends her spare time hiking, reading, and caring for her two small kids.